


Short Shorts and Lingerie

by my_angel_misha



Category: Supernatural
Genre: Anal Sex, Bc they have Daddy issues duh, Blow Jobs, Bottom!Sam, Boys In Love, Daddy Kink, Dean is asleep for a minute but very much wants Sam, Dirty Talk, Felching, First Kiss, First Time, Fluff and Smut, M/M, Masturbation, Mildly Dubious Consent, Panties, Pining, Rimming, Sam is 16, Sammy is a cute twink, Sammy knows what he wants, This is filthy don’t read it around anyone you want to like you, Weecest, cockslut!Sam, dean is 20, flirty!sam, fluff at the end, possessive!dean, top!dean, unestablished relationship
Language: English
Status: Completed
Published: 2018-10-04
Updated: 2018-10-04
Packaged: 2019-07-25 01:39:45
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 3,567
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16187423
Author URL: https://archiveofourown.org/users/my_angel_misha/pseuds/my_angel_misha
Summary: Sammy is 16 years old when he first realizes that his feelings for Dean aren’t exactly conventional. Being a person who always goes after what he wants, Sam starts to wear a little less and flirt a little more in Dean’s presence. He knows what he wants, and he isn’t afraid to fight for it.His big brother happens to be exactly what he wants.





	Short Shorts and Lingerie

**Author's Note:**

> I just wanted to write some weecest, because you can’t stop me. If you’re not into it, don’t read it. If you’re into it, I hope this lives up to your expectations.
> 
> God, I change tenses a lot.

Sam Winchester was sixteen years old when he realized that the feelings he had for his big brother weren’t exactly conventional. He’d always been a bit obsessed with Dean and his attention, but the need for his brother’s approval only deepened as he got older. The innocent admiration Sammy had for Dean when he was younger morphed into something much, much more.

He learned to drive about the same time he learned that he wanted his big brother to fuck him up a wall.

Sam had these dreams about Dean, hotter than any wet dreams he’d ever had before. They were full of steamy, wet pleasure that the younger Winchester craved more than anything else. The thick scent of sex corrupted Sam’s mind, and the dark shape of his brother towering over him on their bed, horny out of his mind, was an image that Sam could never get out of his mind when he woke up. 

It wasn’t normal, but when had anything in the Winchester’s lives ever been normal? They hunted things that most people didn’t even know existed; the most Sam could ask for was his big brother. He just wasn’t sure if Dean felt the same way. 

Sam’s intentions were dirty, sure, but he didn’t want Dean to realize that right off the bat. He wanted Dean’s attraction to him to be a gradual thing, until his brother was so obsessed with Sam that he wouldn’t know what had hit him.

He started wearing a bit less clothing as he’d strut around their shitty motel rooms. Simple things, such as ‘forgetting’ to put on a shirt or coming out of the bathroom with nothing but a towel around his waist. Sometimes Sam swore that he could feel Dean’s eyes on him, if only for a second, but he still wasn’t sure. He needed to be sure. 

Sam started speaking more sweetly when him and his brother were close. He’d peer up to him through long eyelashes, his voice soft and sensual as pink lips would form prettily around his words. He could’ve sworn that Dean's eyes dropped down to his lips on occasion, the gaze gone as quickly as it’d come; Sam still wasn’t sure. 

Then came the touching. 

It was innocent, the act itself, but certainly not the intention behind it. The brothers would sit on the ratty motel couch during late nights and watch movies together, in what Dean referred to as ‘bro time’. Sam would use Dean’s thigh as leverage to stand or lean against him as they watched their movie. Dean didn’t seem too affected, but every now and then Sam would feel a shiver wrack his brother’s body if his fingers ghosted for a millisecond too long. 

And maybe Sam felt the beginning of something in Dean; a little more heat in his gaze, perhaps, or breaths that were held for just a moment too long. He wanted to test that shift. Sam wanted to pull it and stretch it until Dean snapped.

He was at the mall when he devised the next part of his plan, sure that he could break Dean down. The girl at Victoria’s Secret was very sweet to Sam, cooing over him and talking about how much his boyfriend would love the panties he’d picked out. The underwear was overpriced, sure, but there was no price to seeing Dean’s eyes filled with unbridled lust for Sam. 

Sam wore the panties under his summer shorts, the light blue trim peeking out from above the waistband, just a glimpse of the sinful picture of what was underneath. He got all hot and sweaty when they sparred, then complained about how his panties stuck to his skin. Dean’s eyes widened briefly, thrown off just enough that Sam could flip them over and pin his brother down. Sam licked his lips slowly, placing his hands on Dean’s chest and wiggling his hips just slightly before hopping off of his big brother with a soft giggle.

“Got you,” He laughed as he walked away to shower, the bathroom door closing with a teasing click behind him. 

That was the first time that Sam saw Dean’s eyes darken with arousal - for him, no less - and he vowed right then and there, with a hand desperately stroking over his aching erection in the shower, that it wouldn’t be the last time. He came with a choked-off moan, his pretty pink hole clenching around nothing. He would push harder, more aggressively, until Dean would have no choice but to throw Sam down and fuck him like he hated him.  

 

~*~

 

The next day, Sam left their bed early so he could get into the bathroom before Dean. He’d had another dream about his brother that left him hard and leaking, and there wasn’t much he could do about it in their bed, as much as he wanted to. 

He started off with a hand around his cock, but it just wasn’t enough after a while, and his fingers trailed down to the soft rim of his hole. He’d never touched himself there before, but the hard twitch his cock gave when he ran a finger over the tight pucker was more than enough reason to try. 

Sam spread his legs and leaned against the shower wall, slathering shampoo onto his fingers and letting out a shaky breath as he rubbed his index finger along his virgin hole. A sweet moan left his lips as a wet finger slipped inside, his walls soft and inviting as he stroked along them. It was just a tiny bit uncomfortable at first, but he quickly realized how good it felt when his fingers pressed against a bundle of nerves that almost made him jump out of his skin. 

He bit into the flesh of his hand to stop the filthy moan that rose up in his chest, insistantly pushing a second finger into his hole. His fingers fumbled for a moment but he finally found a good rhythm as he began to fuck himself on his hand, breathy moans leaving his lips. Sam scissored himself open, mumbling Dean’s name into his hand like a filthy prayer.

“Dean, Dean, Dean... A-ah, Dean-“ Sam keened, not even realizing that he was doing it. He spread his legs further, the squelch of his fingers pushing into his hole turning him on even more. The teen tried to imagine that his own fingers were Dean’s, thicker and longer and able to reach the spots that would make him scream. 

His free hand clumsily wrapped around his cock, only having to stroke himself a few times before he was coming hard against the shower wall, his hole clenching around his fingers. Sam’s body jerked a few times as he drowned in pleasure, continuing his high, breathy moans of Dean’s name. 

When Sam came down from his high, his mind was fuzzy from his orgasm. He mustered just enough energy to clean up and turn off the water, getting out of the shower and drying off. He pulled on nothing but a pair of pink panties and sweats, drying off his hair until it stopped dripping. 

He absently noticed that Dean was still asleep when he came out of the bathroom, so he slipped back into bed and pushed back against Dean so his brother would curl around his body. A strong arm wrapped around his waist, causing Sam to practically purr as he wiggled back against Dean. 

Sam was about to relax and go back to sleep when he felt something hard and firm press against the small of his back, just above his ass. His mind went blank when he realized just what was pressing against his ass, and a soft moan fell from his lips. He shifted up slightly so Dean’s bulge would press against the plush curve of his ass, rocking his hips with a shaky exhale of breath.  

“D-Dean-” Sam whimpered as he pressed back against Dean even more, grinding his hips against the growing erection that poked at his backside. He yearned for their layers of clothing to disappear, liquid fire shooting down his spine as Dean groaned quietly in his sleep. 

“Sammy, baby...” Dean grumbled deeply, his arm squeezing around Sam’s waist to bring him closer in his sleep. 

And that was all Sam could take without going absolutely insane. He was burning up with need as he began to chant Dean’s name, much like he had in the shower, although this time it was with the intention of waking his brother up.

”Dean, D-Dean... Ah- Wake up, wake up- Fuck me, fuck me, fuck me.” Sam breathed out, turning in Dean’s arms just in time to see panicked green eyes shoot open. 

Dean looked alarmed to say the least, a quick movement indicating that he was going to jump out of the bed. Sam absolutely couldn’t have that, so he crawled on top of Dean, holding him down by the shoulders. 

“De, don’t leave- Please, I... I want you too. I need you so bad. I’ve wanted you for so long, and I’m so horny. I need you inside of me- Need you to fill me up and make me drip your cum, and-“ Sam was cut off by an insistent kiss, feeling more than hearing Dean’s groan. 

Just as Sam was beginning to return the kiss, Dean leaned away with a dark but earnest gaze. 

“Are you sure, Sammy? There’s no turning back from this.” Dean breathed out, needing some sort of approval before he pushed too far and couldn’t come back from it.

“Please, Daddy. I need-“ Sam was cut off yet again by a searing kiss, hearing Dean growl against his lips. The title had just slipped out, but judging by the hard twitch of Dean’s cock, even through their clothing, it seemed his older brother didn’t mind. 

Sam whimpered as he began to kiss Dean back, clumsy and needy and so, so horny. His lower lip was sucked into Dean’s mouth, his older brother’s hands sliding down his back and to the firm globes of his ass.

Dean let out another soft growl, landing a smack to Sam’s ass, which caused the younger brother to break the kiss with a gasping moan. The green-eyed man smirked as he slipped his hands under Sam’s sweats, squeezing his ass through the satin. 

“I’ve seen the pretty panties you wear for me, Sammy. Fuck- It gets me so fuckin’ worked up, baby boy. You have no idea how hard it’s been to keep my hands off of you when I’ve just wanted to bend you over the nearest surface and fuck you until you can’t breathe.” As Dean spoke, his mouth moved across Sam’s neck, kissing and mouthing at the soft skin that was slick with the beginnings of sweat. 

“Please do it- Fuck me.” Sam moaned and let his head fall back, his hips undulating and rolling down against Dean’s. He was so turned on that he was getting dizzy, putting most of his weight on Dean just to stay upright. He listened to his brother’s words and ached for them to come true, whimpering quietly and running his hands down Dean’s chest. 

“Mm... I’m gonna fuck you sweet and slow next time, but for now I just need to make you scream my name. I’ve been waiting too long for sweet and slow- Gonna fill you up with my cum and lick it out of you until your thighs are shaking and you’re begging me to stop.” Dean growled as he smacked Sam’s ass again, savoring the high, breathy moan that left his brother's lips. 

“Oh, please- Please, please do that... I need you so fucking bad, Daddy. Need you to fuck me until I pass out.” Sam whimpered, pulling off his own sweats and panties quickly. 

Dean groaned at the sight, pulling back to lift off his own shirt, and then his sleep pants. His cock was thick and leaking sticky precum that dribbled down the base of his length. He eyed Sam hungrily, like a man who hadn’t eaten in months, or even years. 

Sam’s lips parted as he took in the sight of Dean, his own cock splurting out precum like a leaky faucet. It was the most arousing thing he’d ever seen, and he just wanted to follow the dribble of Dean’s precum with his tongue. 

Never one to deny himself anything, Sam slithered down Dean’s body and wrapped a hand around his cock, watching his brother’s eyes go dark at the revelation. 

“You’re so big, Daddy- Wonder if you can make me choke on your thick cock.” Sam breathed out, licking messy stripes up Dean’s cock with his soft pink tongue. He moaned quietly at the taste, mouthing his way up to the head, where he sucked hard, eager to taste another rewarding spurt of Dean’s precum. 

He took Dean in slowly, his lips suctioned to his shaft as he slid his mouth down about halfway. Sam felt Dean’s cock bump the back of his throat and pushed even further, until about an inch was pushed into his wet throat. He swallowed around the head, feeling Dean convulse under him. 

“Baby, I’m not gonna last in your mouth- Wanna fuck you so bad.” Dean breathed out, twisting his fingers in Sam’s hair and pulling him none too gently off his cock. 

Sam moaned out his loss, his lips spit-slick and reddened from abuse. He quickly realized how much more he wanted Dean inside of him, though, and nodded quickly. 

“C’mon, get inside of me.” Sam rolled off of Dean and onto his hands and knees, arching his ass up so his brother could get an eyeful of his fluttering hole, still wet from being fucked by his fingers in the shower. “I’m already fucked open for you, Daddy. Push your cock inside of my hole- It’s all for you.” 

Dean groaned at the sight, having to grip the base of his cock to stave off his orgasm. He grabbed ahold of Sam’s cheeks, pulling them apart so he could push his face between them, licking into his hole. 

Sam let out a keening moan, feeling his legs give out as Dean’s tongue pushed into his wet hole. He pressed back against his face, making filthy noises as he spread his legs even further for Dean. 

Dean ate Sam out like he was the last meal he’d ever get, licking and sucking and nipping until his little brother was a blubbering mess of moans and pleas. Even then, he continued for another long minute, lapping at Sam’s soft inner walls and sucking at his rim. 

“Please, please, please, I-“ Sam broke off in a sob, blissed out as tears began to run down his flushed cheeks, begging shamelessly for his big brother’s cock. “Please, I need you- Fuck me, fuck me, Daddy...” 

“Anything for you.” Dean simply couldn’t wait any longer as he pulled his mouth away from Sam’s now soaked hole, saliva running down the boy’s taint. He guided his cock to Sam’s entrance, beginning to push in without preamble. There was a little resistance, and he kept his initial movement slow as he worked to bottom out. 

“A-ah-“ Sam gasped as the fat head of Dean’s cock pushed into his body, the action resounding in a filthy noise that made Sam’s cock jerk hard. He shook and whimpered as Dean continued to push in, inch by agonizing inch, until he was fully sheathed in Sam’s pliant body. 

“Shh, baby boy... I’ve got you. Give it a minute.” Dean breathed out, having to use every ounce of self-control he had not to start fucking into Sam’s vise-like heat immediately. It felt like his little brother's hole was leaking, so wet and pliant around his throbbing cock.

Sam nodded and made sweet little whimpering noises, not needing more than a minute before he began to rock back against Dean. He was unable to bear it, needing both the pain and the pleasure of Dean’s thick cock splitting him in half.  

“Do it, Daddy- Fuck me as hard as you can.” Sam breathed out, eager and more impatient than he’d ever been before - which was saying something, because he was one impatient teen. 

“Anything for you.” Dean whispered in Sam’s ear, tugging at the lobe with his teeth. He began to pull out of Sam, almost all the way, before shoving back in roughly. 

Sam let out a loud moan of Dean’s name, throwing his head back and gripping at the bedsheets. He felt himself drooling a little against Dean’s pillow, inhaling the musky scent of his brother that still lingered there. 

From then on, Dean’s cock was all he could think about. His big brother was wrecking him, fucking the younger boy as if he absolutely despised him. His thrusts were hard and sharp, hitting Sam’s prostate each time, working loud moans out of his little brother. 

“Dean! Daddy, please- I can’t hold on... I can’t-“ Sam whimpered, rocking back against every thrust like he just couldn’t handle the thought of ever being empty again. He let out hiccuping sobs against Dean’s pillow, biting into the fabric so he wouldn't grind his teeth together. 

Dean just fucked harder and harder into Sam’s sweet little hole, growling out disgusting filth into his brother’s ear. He wasn’t going to last much longer either, his orgasm creeping up on him. 

“You gonna come just from Daddy’s cock splitting you open? Gonna fill you up until you’re dripping with my cum- Gonna lick it all out of you and make you kiss it out of my mouth. You want that, baby? You want Daddy to make a mess of your slutty little hole?” Dean growled, sucking deep, blooming bruises onto Sam’s neck. 

Sam nodded eagerly, absolutely overwhelmed with pleasure, his orgasm building hot and heavy in his abdomen. Every rough thrust brought him closer and closer to the edge, his body feeling as if it would explode once he finally reached his climax. 

The teen finally couldn’t last any longer when Dean grinded into him, hard and deep, to massage his prostate with the spongy head of his cock. With a scream of his brother’s name, Sam released onto the bed, his hole clenching down like a vise around Dean. 

Dean came with a low groan, his hips stuttering as Sam’s hole milked him for everything he had. He was so blissed out, his little brother's soft cries of pleasure only intensifying his high. 

Once they both calmed down a little, Dean pulled out of Sam’s body and admired the dribble of cum that leaked from his abused hole. 

“Wanna taste you.” Sam made a quiet whining noise and wiggled his ass lazily, clenching his hole to try and keep everything inside, to no avail. 

Dean groaned softly and leaned to lick up the trail of cum that leaked down Sam’s milky white thigh, turning his brother around so he could kiss his lips.

Sam let out a content puff of breath, curling his tongue into Dean’s mouth to lick out his salty-sweet release. He sucked it off of Dean’s tongue, curling closer like a cat. 

Once the teen was content and absolutely exhausted, he leaned away from the kiss and smiled lazily up towards Dean. 

“I think you broke me.” Sam giggled breathily, cuddling up to Dean and sighing happily when his big brother’s arms wrapped around his waist. He nuzzled into Dean’s neck, smiling as he nosed over his pulse. 

“Yeah? Well, I think we both had fun breaking you.” Dean laughed quietly, pulling the blankets up over them so they could cuddle closer. 

Sam opened his mouth to answer, but only sighed contently as he began to drift off, absolutely exhausted from the mind-blowing orgasm. 

“Love you, Sammy... Sleep well.” Dean whispered as he stroked gently through Sam’s soft hair, watching him with a loving gleam in his eyes. 

Sam’s lips curled up in response before he completely passed out, dead to the world for a long while. He dreamt of his big brother taking him out on a date, anything but ashamed of their relationship; in fact, dream Dean was extremely proud of Sam, showing him off whenever he could. 

Even if Sam’s dream wasn’t a reality, some part of him blossomed into hope, warm and happier then he’d ever been. He felt as if this was the start of something new, and he absolutely couldn’t wait to see everything that the future held for Sam and Dean Winchester. 

When he woke up, Dean was asleep, his chest rising and falling in long, peaceful breaths. Sam admired Dean’s features, running his thumb over his freckled cheek with a smile. 

“Love you too, De... Love you with my whole heart.” Sam whispered and closed his eyes again, curling up closer to Dean and inhaling his musky scent.

He felt like nothing could ever hurt him while he was in his big brother’s arms, and the thought alone caused Sam to drift back off to sleep, happier than he’d ever been in his whole life. 

As he fell asleep once again, the words ‘love’ and ‘forever’ rambled around in his head, giving him a beautiful hope for the future and whatever lied ahead. 

It was him and Dean against the world, after all, and together, nothing could stop them.  

**Author's Note:**

> I live and breathe for comments <3
> 
> Yikes, this is the filthiest thing I’ve ever written I feel like I need to wash my hands just to get the filth off.
> 
> As usual, sorry for any mistakes! I’ll proofread this in the morning when it’s not 3:51 am.
> 
> I made dumbass mistakes, but I fixed them.


End file.
